Summer explorations, part one: A feeling of relative control.

Summer traditionally seems to be a great time to muck around with my systems and workflows. Lots of people are away, so the office gets these nice little lulls where I can sit quietly for bits of time and ruminate. We’re on the cusp of a new iOS release–and new hardware–but nothing is happening quite yet, so I’m thinking about it, but also can’t act on anything. Year after year (if I read back through blog posts and journal entries), I end up tugging on threads in my setups over and over again, exploring things I’ve used for months or years, trying new things, generally comfortable with upending everything, knowing in September I’ll be wiping everything and installing iOS fresh.

This summer’s been no different, apart from me being way busier than normal at work. But ironically, it’s been this shift that’s precipitated probably some of the biggest changes and realizations about the way I organize and deal with information in my life. In fact, the changes in my responsibilities have triggered a chain of events that will likely alter the way I deal with information for a long time.

It came in phases. Phase one involved creating a calculated division between my work and personal worlds, which didn’t exist before. Phase two built on phase one and is all about how I think about doing things in my personal life, and how I structure the things I need to remember, the things I want to accomplish, and just about everything else that makes its way into my brain.

But I’ve come out (what I think is) the other side now, and the crazy part is: sure, I’ve played with some apps and done some reconfiguration of tools, but in doing the things I’ve done this time around, I’ve uncovered some things that I didn’t expect to.

We’ll get to that.

This is all probably too long and meandering to walk through in one post, so I’m going to break it up. Gotta get those 16 page views somehow. Fair warning, this is some nerdy-ass stuff.

Let’s begin.


Since joining a much larger company, the things I need to do–and subsequently keep in my mental RAM–have changed dramatically. I interact with many, many more people, on a global scale, across time zones, in different disciplines, and with greatly varying agendas and goals. It’s actually been an incredibly good experience for me as a person because it’s opened me up to thinking about things in new ways, and given me the opportunity to work with lots of personalities I might not have been exposed to otherwise. All good things.

Along with this comes a lot of new stuff I need to do and think about. I lead a small team doing interesting projects, but I also play roles in other parts of the company as well. I have to span a lot of different activities in the course of any given day, and I may not have time to cover everything I need to. I have had to learn to delegate and share some of the load, which honestly was a challenge for me, but utterly necessary in order to keep my sanity. Luckily for me, my team is amazing and is more than willing to help out with anything.

So instead of keeping my tasks in a silo by themselves, we’re all using Todoist together now. It has been transformative, mostly because I’ve never used it with anyone before. 1 I’ve used it extensively myself, but the service begins to take on a whole new life when you use it with other people. So we all have the app installed, and the team has access to just about every project in my personal list. This way, they can see everything I’ve got going on, can jump in and handle things if they see an opportunity to do so, and I can assign tasks to them as I work through setup of projects on calls and in meetings. I get notifications when things get done, and we can comment on tasks, attach files, and chip away at large bodies of work all at the same time. It’s been terrific for feeling like we’ve got a handle on everything we need to do, and I’m glad I kept my premium account active, because it’s really been quite handy.

However, now that I’m sharing all this stuff in Todoist, I’ve discovered that I want to have the things I’m tracking in my personal life somewhere else. The other part of joining a large company is stuff like IT policies and compliance, and I’ve found that having a clean separation of work and personal data on my company-provided laptop is the most comfortable way for me to work. It also gives me another reason to bring my iPad to work every day, which is essentially my personal laptop now anyway.

So I’ve split my world: email in different apps (Mail for work, connected to Exchange, Airmail for personal), files (Box for work, Dropbox for personal, along with my Synology), and tasks (Todoist for work and a million freaking things in the last month for personal stuff). For some reason, my calendar is the only thing I don’t mind blended, although I tried that too for a while (Calendar for work, Fantastical for personal).

I’ve never done this before; work and personal life was always together, and not in an unhealthy way. When you help start a company, it kind of happens. You don’t draw those boundaries the same way you might when you’re not personally invested in something. It never bothered me to see that stuff all mashed up–in fact, I really liked figuring out how to filter and sort in creative ways. Some of my best tinkering has been around how to use my favorite tools to show me exactly what I wanted when I wanted it. Now I’ve realized with all the things I’m tracking, the best way to do that and accommodate my personal wishes to keep work and personal life connected but separate means I take that information and split it right down the middle.

With certain data, like email, this was easier than I’d expected. I always thought having a unified inbox was wonderful, until I was sifting through dozens of work emails to lift out the actually important personal email about my mortgage that I absolutely couldn’t afford to miss. So I bought Airmail and haven’t looked back. It got a great update right around the time I was making this change, so it was rather fortuitous.

Files were easy too. I keep one folder from Dropbox on my work machine called “Sync” and it only contains a dedicated 1Password vault I use for work stuff, and my Alfred data. Everything else on that machine is work stuff and so it lives in Box.

Tasks. That’s where things take a real turn. Big surprise, I know.

Next post: the clouds part, I go a little crazy, and land right back where I always start, a little more enlightened for the journey. As it should be.


  1. Federico has written quite a bit on using Todoist with his team at MacStories, and they do some very cool stuff over there with it and a few other tools. 

Things I like this week, volume 26.

Catalyst Case for Apple Watch

I’m a longtime fan of Casio G-Shock watches. I have an Apple Watch because I like the idea of smartwatches, and because it works with my iPhone the best. I’ve never particularly liked the way it looked, but I was willing to make a fashion trade off for functionality. It obviously has the best feature set of any watch I can pair with my phone, but it looks like a space lozenge. I mean, if you’re a fan of watches, it really probably isn’t doing anything for you. But it does do a lot of crap.

Anyway, I found this and it’s basically the exact kind of style I want in a watch (chunky, rugged, metal + plastic, colors optional; round) but isn’t out until this fall. It does surf forecasts (yes!) but runs Android Wear (I can use that with an iPhone, sort of, right?!), which may or may not provide what I need/want from my smartwatch. It’s also as much as an Apple Watch, so I’m not sure I want to take that dive. Maybe. I don’t know.

In the meantime, I’ve made an aesthetic upgrade to my setup, by adding this chunky-ass case. I’d heard of Catalyst, because I always buy waterproof cases for my phones (usually Lifeproof), primarily for beach/vacation action, but was unaware they also made a product of similar pedigree for Apple Watch.

I wanted a (smart)watch I could take surfing with me, but they explicitly say you shouldn’t engage in “high-velocity water activities” with the case. I don’t know if two-foot waves on a longboard at the Jersey Shore qualify as “high-velocity”, but hey, who am I to challenge a manufacturer on their product constraints. But I thought I might be able to get away with it, since most of the time I’m not surfing, and it definitely beefs up the Apple Watch in a decent way.

Overall, I think it’s pretty great. I definitely like having a bigger watch, and it is a bit more rugged looking. Because of the shape of the Apple Watch, it’s limited to a larger version of that vertical rectangular layout, but it adds a nice extra bulge on the side where the crown and button sit, which does change the overall shape in an interesting way. I’m not in love with the band, which is soft silicone–don’t get me wrong, it’s insanely comfortable but because of the finish of the rubber, it slides out of its loop quite a bit (the little ring that holds the extra bit of watch band down, I mean), so I end up flappin’ in the breeze a little more than I would like.

But it’s more in line with the kind of look I want, and it does add some extra water resilience, so I’m pretty pleased with it. Not too bad to take on and off, but you definitely won’t be switching bands quickly. You’ll need a few minutes to undo the case and get the watch out, but it’s not hard: a single tiny screw and a pair of snap hinges, and you’re done. I haven’t put it through its paces in terms of durability because it’s so new, but for looks, it certainly meets my criteria.

Catalyst Case for Apple Watch